(4-苄氧基苯氧基)乙酸甲酯 | 81466-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-苄氧基苯氧基)乙酸甲酯
• 英文名称: (4-benzyloxyphenoxy)acetic acid methyl ester
• 英文别名: methyl 2-(4-(benzyloxy)phenoxy)acetate；(4-Benzyloxy-phenoxy)-acetic acid methyl ester；methyl 2-(4-phenylmethoxyphenoxy)acetate
• CAS: 81466-35-5
• 化学式: C₁₆H₁₆O₄
• mdl: MFCD12025125
• 分子量: 272.301
• InChiKey: ADGZLDOOBYGSJV-UHFFFAOYSA-N

物化性质

• 沸点：
  397.8±22.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.187
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-苄氧基苯氧基)乙酸甲酯 在 lithium hydroxide monohydrate 、 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 51.0h， 生成 N-[(2,6-difluorophenylcarbamoyl)methyl]-2-(4-hydroxyphenoxy)acetamide
  参考文献：
  名称：

  In silico and pharmacological screenings identify novel serine racemase inhibitors

  摘要：

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.

  DOI：

  10.1016/j.bmcl.2014.07.003
• 作为产物：
  描述：

  4-苄氧基苯酚 、 溴乙酸甲酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以89%的产率得到(4-苄氧基苯氧基)乙酸甲酯
  参考文献：
  名称：

  In silico and pharmacological screenings identify novel serine racemase inhibitors

  摘要：

  D-Serine is a coagonist of the N-methyl-D-aspartate (NMDA)-type glutamate receptor and its biosynthesis is catalyzed by serine racemase (SR). The overactivation of the NMDA receptor has been implicated in the development of neurodegenerative diseases, strokes, and epileptic seizures, thus, the inhibitors of SR have potential against these pathological states. Here, we have developed novel inhibitors of SR by in silico screening and in vitro enzyme assay. The newly developed inhibitors have lower IC50 value comparing with that of malonate, one of the standard SR inhibitor. The structural features of novel inhibitors suggest the importance of central amide structure having a phenoxy substituent in their structure for the SR inhibitory activity. The present findings suggest the importance and rational development of new drugs for diseases of NMDAR overactivation.

  DOI：

  10.1016/j.bmcl.2014.07.003

文献信息

• Benzyloxy derivatives as MAOB inhibitors
  申请人：Jolidon Synese

  公开号：US20050288367A1

  公开（公告）日：2005-12-29

  The invention relates to compounds of the formula and their pharmaceutically acceptable salts wherein R 1 , R 2 , R 3 , R 4 , R 5 , n, m, and o are as defined in the specification. The compounds are selective monoamine oxidase β inhibitors and are useful for the treatment and prevention of Alzheimer's disease and senile dementia, as well as other CNS disorders. The invention also relates to processes for preparing such compounds and pharmaceutical compositions containing them.

  这项发明涉及以下公式的化合物及其药学上可接受的盐，其中R1、R2、R3、R4、R5、n、m和o如规范中所定义。这些化合物是选择性单胺氧化酶β抑制剂，对治疗和预防阿尔茨海默病和老年性痴呆症以及其他中枢神经系统疾病有用。该发明还涉及制备这类化合物的方法和含有它们的药物组合物。
• FUNCTIONALIZED DIPHENOLICS AND ABSORBABLE POLYMERS THEREFROM
  申请人：Bezwada S Rao

  公开号：US20070135355A1

  公开（公告）日：2007-06-14

  The present invention relates to dephenolic compounds, an example of which is shown below, which are functionalized, and polymers formed from the same. Polymers formed from the functionalized diphenolics are expected to have controllable degradation profiles, enabling them to release an active component over a desired time range. The polymers are also expected to be useful in a variety of medical applications.

  本发明涉及去酚化合物，以下是一个示例，这些化合物被官能化，并且形成的聚合物。从官能化二酚形成的聚合物预计具有可控的降解特性，使它们能够在所需的时间范围内释放活性成分。这些聚合物也预计在各种医疗应用中有用。
• Functionalized phenolic esters and amides and polymers therefrom
  申请人：Bezwada S. Rao

  公开号：US20060173065A1

  公开（公告）日：2006-08-03

  The present invention relates to a compound of the formula: R-AR—O—Y—R′ Wherein R represents one or more members selected from H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid, —NO 2 , —NH 2 , —NHCOCH 3 , and —NH—Y—R′, which is attached directly to AR or attached through an aliphatic chain. The carboxylic acid moiety in R includes but is not limited to the following carboxylic acids: benzoic acids, cinnamic acids, ferulic acid, caffeic acid, syringic acid, salicylic acid, vanillic acid, phenylacetic acids, phenylpropionic acids, and sinapinic acid. -AR—O— is a biologically active phenolic moiety comprising 1 to 6 substituted or unsubstituted aryl rings that are directly bonded to each other, fused together, or joined through a linking group. Y represents a member selected from: —COCH 2 O— (glycolic ester moiety) —COCH(CH 3 )O— (lactic ester moiety) —COCH 2 OCH 2 CH 2 O— (dioxanone ester moiety) —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester moiety) —CO(CH 2 ) m O— where m is an integer between 2-4 and 6-24 inclusive —COCH 2 O(CH 2 CH 2 O) n — where n is an integer between 2 and 24, inclusive; and R′ is either hydrogen or a benzyl or an alkyl group, the alkyl group being either straight-chained or branched. The resultant functionalized phenolic compounds, used singly or in combinations, and their polymers have controllable degradation profiles, releasing the active component over a desired time range. The polymers are useful for biomaterials and biomedical devices, wherein said biologically active phenolic moiety is a residue of a phenolic compound.

  本发明涉及一种化合物，其化学式为：R-AR—O—Y—R′，其中R代表从H、烷氧基、苯甲氧基、醛基、卤素、羧酸、—NO2、—NH2、—NHCOCH3和—NH—Y—R′中选择的一个或多个成员，该成员直接附着在AR上或通过脂肪链连接。R中的羧酸基团包括但不限于以下羧酸：苯甲酸、肉桂酸、阿魏酸、咖啡酸、槲皮酸、水杨酸、香草酸、苯乙酸、苯丙酸和芥子酸。-AR—O—是一个生物活性的酚基团，包括1到6个取代或未取代的芳香环直接连接、融合或通过连接基团连接的环。Y代表从以下成员中选择：—COCH2O—（乙二醇酯基团）—COCH(CH3)O—（乳酸酯基团）—COCH2OCH2CH2O—（二氧环酮酯基团）—COCH2CH2CH2CH2CH2O—（己内酯酯基团）—CO(CH2)mO—其中m是2-4和6-24之间的整数—COCH2O(CH2CH2O)n—其中n是2到24之间的整数；R′是氢或苄基或烷基，烷基可以是直链或支链。所得的功能化酚类化合物单独或组合使用，其聚合物具有可控的降解特性，释放所需时间范围内的活性成分。该聚合物对于生物材料和生物医学器械有用，其中所述的生物活性酚基团是酚类化合物的残留物。
• FUNCTIONALIZED PHENOLIC ESTERS AND AMIDES AND POLYMERS THEREFROM
  申请人：Bezwada Rao S.

  公开号：US20110130448A1

  公开（公告）日：2011-06-02

  The present invention relates to a compound of the formula: R-AR—O—Y—R′ Wherein R represents one or more members selected from H, alkoxy, benzyloxy, aldehyde, halogen, carboxylic acid, —NO 2 , —NH 2 , —NHCOCH 3 , and —NH—Y—R′, which is attached directly to AR or attached through an aliphatic chain. The carboxylic acid moiety in R includes but is not limited to the following carboxylic acids: benzoic acids, cinnamic acids, ferulic acid, caffeic acid, syringic acid, salicyclic acid, vanillic acid, phenylacetic acids, phenylpropionic acids, and sinapinic acid. -AR—O— is a biologically active phenolic moiety comprising 1 to 6 substituted or unsubstituted aryl rings that are directly bonded to each other, fused together, or joined through a linking group. Y represents a member selected from: —COCH 2 O— (glycolic ester moiety) —COCH(CH 3 )O— (lactic ester moiety) —COCH 2 OCH 2 CH 2 O— (dioxanone ester moiety) —COCH 2 CH 2 CH 2 CH 2 CH 2 O— (caprolactone ester moiety) —CO(CH 2 ) m O— where m is an integer between 2-4 and 6-24 inclusive —COCH 2 —O—(CH 2 CH 2 O) n — where n is an integer between 2 and 24, inclusive; and R′ is either hydrogen or a benzyl or an alkyl group, the alkyl group being either straight-chained or branched. The resultant functionalized phenolic compounds, used singly or in combinations, and their polymers have controllable degradation profiles, releasing the active component over a desired time range. The polymers are useful for biomaterials and biomedical devices, wherein said biologically active phenolic moiety is a residue of a phenolic compound.

  本发明涉及以下式的化合物：R-AR-O-Y-R′其中R代表从H、烷氧基、苯甲氧基、醛基、卤素、羧酸、-NO2、-NH2、-NHCOCH3和-NH-Y-R′中选择的一个或多个成员，它们直接连接到AR或通过脂肪链连接。R中的羧酸基团包括但不限于以下羧酸：苯甲酸、肉桂酸、香豆酸、咖啡酸、槲皮酸、水杨酸、香草酸、苯乙酸、苯丙酸和芥子酸。-AR-O-是一个生物活性酚基团，包括1至6个取代或未取代的芳环，它们直接连接在一起，融合在一起或通过连接基团连接在一起。Y代表从以下成员中选择：-COCH2O-（乙二醇酯基团）、-COCH（CH3）O-（乳酸酯基团）、-COCH2OCH2CH2O-（二氧杂环酮酯基团）、-COCH2CH2CH2CH2CH2O-（己内酯酯基团）、-CO（CH2）mO-其中m是2-4和6-24之间的整数，-COCH2-O-（CH2CH2O）n-其中n是2至24之间的整数；以及R′是氢或苄基或烷基，烷基可以是直链或支链。所得的功能化酚化合物，单独或组合使用，及其聚合物具有可控的降解特性，可以在所需的时间范围内释放活性成分。这些聚合物对于生物材料和生物医学器件非常有用，其中所述的生物活性酚基团是酚化合物的残基。
• SERINE RACEMASE INHIBITOR
  申请人：National University Corporation University of Toyama

  公开号：US20140371291A1

  公开（公告）日：2014-12-18

  A novel serine racemase inhibitor exhibits sufficient activity and specificity. The serine racemase inhibitor includes one or more compounds selected from compounds respectively represented by the following general formulas [MM_1], [DR_1], [DR′_1], [LW_1], and [ED_1] as an active ingredient.

  一种新型的丝氨酸外消旋酶抑制剂表现出足够的活性和特异性。该丝氨酸外消旋酶抑制剂包括一种或多种选自以下通用式[MM_1]、[DR_1]、[DR′_1]、[LW_1]和[ED_1]所代表的化合物的化合物作为活性成分。